


Is That A Flirtation?

by MakennaSweets1967



Category: Supernatural
Genre: Awkward Flirting, Bad Flirting, Castiel Has Feelings for Dean Winchester, Castiel/Dean Winchester First Kiss, Dean Winchester is Bad at Feelings, Flirty Dean Winchester, M/M, Mutual Pining
Language: English
Status: Completed
Published: 2020-07-21
Updated: 2020-07-21
Packaged: 2021-03-04 22:28:47
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,873
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25423918
Author URL: https://archiveofourown.org/users/MakennaSweets1967/pseuds/MakennaSweets1967
Summary: Dean Winchester teaches Castiel how to flirt. Don't tell Sammy!
Relationships: Castiel/Dean Winchester
Comments: 2
Kudos: 65





	Is That A Flirtation?

**Author's Note:**

> I'm currently perishing.

Since the beginning of time, Castiel watched the greatest love stories of all time. Watching people plummet into a feeling that angels weren't supposed to feel. The way the drew together calling themselves soulmates, their other half, and so on. 

Even though he watched over humanity glimpsing at thousands of love stories he couldn't understand how they did it. 

Sure falling for Dean was easy, but his love is unrequited. Maybe he could find comfort somewhere else as Sam and Dean do. 

Castiel watched Sam, and Dean, swoon a girl without effort. When he tried to swoon someone it always ended in failure. 

Cas frowned looking at his hands as Sam snuck away to another hotel room with someone. Luckily Dean hadn’t found anyone tonight. 

”Are you good?” Dean asked sliding a beer across the table to Cas. 

“Yeah” Cas deflected something he picked up from Dean. 

Dean didn’t bother with his drink instead, leaning forwards to examine the distressed angel “Come on man I know you, what’s going on?” 

Cas looked into Dean’s green eyes assuring him ”I don't understand flirtation.” 

”Flirtation?” Dean threw his head back in laughter, he loved Cas’s strange mannerisms sometimes. 

”Never mind” Cas huffed crossing his arms over his chest, his eyes turning cold. He is an angel he doesn't need human connection anyways. 

Looking at Cas’s taut face, Dean took a swig of beer ”Cas” he drawled out ”Look what do you mean?”

There was something comforting about how Dean gave Cas time to gather his thoughts ”Angels aren't supposed to have feelings, and intimacy, but... I want those things. I just I'm not like you and Sam I don't understand human interaction.” 

Dean took in what his best friend was saying a boyish grin playing on his lips ”You mean picking up chicks.”

Cas cocked his head to the side, squinting his eyes ”I can pick up newborn chickens just fine Dean, I don't know how to flirt.” 

”That's what I -” Dean began before cutting himself off no bother explaining things ”Never mind. I can help you with that. Grab your coat cause you aren't going to be a virgin anymore” 

Baffled by Cas’s declarations Dean offered to help him without thinking. Possibly his attempt at pushing his feelings for Cas aside. Or that he felt the need to push him into someone else because in his twisted mind it was easier to accept him loving someone else than to know the truth; he could never deserve Castiel’s love. Or maybe it was just that he was a glutton for torture and pain. 

Pulling up to a bar, Dean looked over at Cas ”Alright just go up to a woman... Or man whatever your style. Then compliment them, smile.”

”Okay” Cas hopped out the car strolling in he spotted a girl leaning against the bar with a drink. She is pretty with a short brown pixie cut and tattoos down both arms. 

Dean looked over to the girl he likes them tall, check he thought ”Her”

Cas nodded he didn't have a type other than Dean but he could tell she had a good soul. 

”Okay I'll be over here show me what you got,” Dean said pulling a chair out by the bar close enough to slightly hear. 

Trenchcoat flapping as he walked over to the girl, Cas tapped on her shoulder ”hello.”

”Hi there” The girl gave a coy smile turning around. Cas did have a good taste. Still, he stood there looking uncomfortable, the girl drawing her eyebrows together in confusion ”I’m Kennedy” 

”Cas, I'm Castiel” looking beyond uneasy Cas continued lowly. Dean couldn't make out what he was saying but just as soon as their conversation began it ended. 

”Alright Dick I'm going to go then” Kennedy scoffed, looking at Cas like he’d grown three heads. 

”Oh... Okay” 

Returning with a defeated look, Cas dropped his eyes to the floor ”What happened man” 

”I was trying to compliment her hair and she called me a dick and left. I don't understand I do have male genitals but -” 

”whoa” Dean slapped a hand over Cas’s mouth, he spent enough time thinking about that he didn't need more ”Here I’ll show you how to flirt just don't mention this to Sammy”

”Of course”

”Just do what you did now but try to look less like you have a stick up your ass. Ask them would you like a drink” Dean winked at Cas flirtatiously, ”see” 

”I see the point is to arouse them,” Cas asked bluntly leaning closer to Dean winking ”Like this” 

Dean bit his cheek almost drawing blood ”exactly” 

He could barely breathe, yet he placed his arm up on the table daring to lean closer to Cas. The two of them just looking at each other leaned in slightly against the bar. 

”Try to make contact with the person,” Dean said dragging his fingers lightly down Cas’s arm ”Unless they don't want it then stop” 

”oh, like holding hands in movies,” Cas asked his voice uneven, Dean could feel the tingles in his fingertips. He knew he was playing a dangerous game. 

”Yeah, and when you have talked for a while lean in for a kiss” Dean whispered inches away from Cas’s face. God, he could smell the intoxicating scent of honey dripping from him ”Always hesitate so they have time to back away” 

Cas nodded his cheeks flush at their closeness, he wasn't sure if this was supposed to torment him or not. He felt his eyes flutter close before Dean pulled away. 

”Um, yeah” Dean coughed his cheeks brightly red, Cas’s eyes snapped open. His lip wobbling, ”Pretend like I'm someone you're interested in and show me what you got” 

Cas got up walking away before coming back, he slid into the seat beside Dean ”hi there I'm Castiel”

”I’m Dean” he grinned. 

It wasn't hard to show Dean he was interested, although the flirting wasn't his strong suit. 

”Your soul is radiant” Cas breathed looking into Dean’s deep green eyes. His posture dipping towards Dean. 

Dean sucked in a breath, begging his voice to not betray him ”That’s good, but maybe try physical features that humans can see” 

”Oh I forgot,” Cas said, leaning back in his chair. 

Dean clasped a hand over his shoulder ”Nah man it was good now get out there”

Yet again Cas failed coming back with a small frown. So Dean gave him more pointers and once again he did well flirting with Dean. 

”I don't get it, man, you do fine with me and then you crash and burn,” Dean says rubbing the back of his neck exasperated. 

Cas dropped his hand from Dean’s face where he was trying something new ”I’m sorry Dean we should just go.”

”No man” Dean paused ”Just pretend like the person is me, err that's not what I mean. Just pretend like you are comfortable around them.” 

The first idea sounded good maybe it would suit him to think of Dean while flirting ”I understand” 

”Good” Cas felt him pat his back as he walked up to a guy with a sharp jaw and dirty blonde hair. He resembled Dean a little bit. 

”Hi, I'm Castiel” Cas smiled swiping his tongue on his lips. Looking at the man his eyes were full of life, brighter than Dean’s. 

”Hello Castiel” he winked, inviting him to sit at his table ”Tom”

”Would you let me buy you a drink” Cas offered sitting down but edging close to him. 

”Well you are cute but are you sure your boyfriend wouldn't mind,” Tom says raising an eyebrow pointing to Dean. 

”Huh” Cas did his little head tilt, looking towards Dean who was glancing every so often at them ”Oh no, Dean doesn't like me like that. He was teaching me to flirt.” 

Tom nodded ”Ah, well he's good then” 

Cas laughed, he could still feel Dean’s soft touches ”yeah” 

Dean watched as the awkwardness faded between Cas and the guy he started talking too. His shoulders hunched over, he took another long sip from his beer bottle. 

Hearing the man howl with laughter, Dean felt a pang in his chest. He is an idiot and a coward. Finishing off the beer he glanced at the two one last time. They seemed happy, he got up walking out of the bar. He leaned against the exterior wall letting out a shaky sigh. Had he lost Cas forever?

Cas saw Dean leave from the corner of his eye, he seemed saddened and all he wanted to do was heal him. Even as Tom told him a joke he couldn't help but want to go after Dean. 

”Castiel, you don't actually want to flirt with me, do you. Are you dreaming I'm someone else.” Tom asked with a careful measure. Looking towards the bar door, where Dean just walked out of ”Like your friend who I resemble”

”I’m sorry” 

Tom gave him an understanding look ”It’s okay I've dated a few people that were in love with someone else. You should just tell him because you can't find comfort in someone else until you get over him.”

”You are very wise” Cas smiled pushing himself out of the chair ”but I can't tell him, because he could never love me in return.” 

”Good luck anyways Castiel” 

”Goodbye Tom” 

Cas pushed open the bar’s door, somehow he felt better. Even though nothing changed. 

”What are you doing here” Dean called out from beside the door. Still, relief flooded his senses, even a bit of happiness that Cas didn't go home with someone else ”I thought you were doing well” 

”It didn't work out” Cas shrugged, standing in front of Dean. 

”Oh come we’ll find you someone” he directed Cas back towards the inside. Not sure why though he was relieved to have him back, and now he was pushing him away again. 

Cas didn't move ”Stop Dean I don't want to” 

”Don’t be like that” Dean snapped frustrated by the tension in his mind. 

Flinching back like he’d been punched by Dean’s words, Cas snapped back in a cold voice ”I’m done, Dean. I don't want to be with those people.” 

”Don’t pull that angelic, I don't need love BS” Dean yelled invading Cas’s space his breath hot on his face. 

Cas could smell the alcohol on his breath, he threw Dean against the brick wall. His arm pressed against his chest holding him down ”It’s not about me being an angel. It's that the only person I want to love me is you” 

His voice cracked, tears barrelling against the back of his eyes. 

Dean looked at Cas in shock, no air going in or out of his lungs. He brought a hand up stroking down the side of Cas’s face with the back of his hand. 

Cas melted into the delicate touch, loosening his hold on Dean with his arm. He could stop looking at the love in Dean’s eyes surrounded by caution and vulnerability but there nonetheless. 

”Can I kiss you?” Dean whispered their faces inches apart for the second time tonight. Cas nodded. 

This time when his eyes fluttered shut, he was met with a pair of warm lips.

**Author's Note:**

> Thank you for reading I hope you enjoyed it! Please leave feedback or something you would like me to write! Stay strong and keep fighting.  
> \- Makenna Sweets


End file.
